


Relationships Are Weird

by iDiru



Category: Supernatural
Genre: Anal, Anal Fingering, Come Eating, Come Sharing, Destiel - Freeform, Friends With Benefits, Incest, Jealousy, M/M, Multi, Oral, Threesome, Wincest - Freeform, Wincestiel - Freeform
Language: English
Status: Completed
Published: 2014-02-28
Updated: 2014-02-28
Packaged: 2018-01-14 02:23:13
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,956
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1249189
Author URL: https://archiveofourown.org/users/iDiru/pseuds/iDiru
Summary: <blockquote class="userstuff">
              <p>Castiel discovers modern relationships aren't so straight forward when Dean invites someone else into the bedroom.</p>
            </blockquote>





	Relationships Are Weird

                Relationships were a strange thing, to an angel who had spent most of his life without one. But he had assumed a relationship was one between two people. Where they loved each other, had sex, and did things together. Though apparently, this was not always the case. It had been, for some time though. Castiel had remembered that first kiss; stolen from him in the dark of the night, followed by many more until a few nights ago he’d had his virginity taken from him by none other than the man he’d rescued from Hell. Though he was still a virgin, he was still new to the whole…sex thing. Dean had taken him at least twice, counting his first time, but he still found the pleasure to be somewhat overwhelming. Castiel really had no idea what to call their relationship; were they _actually_ in a relationship? He had assumed so, until one night things seemed to change and something the angel had never anticipated happened.

 

                It had started innocently enough, the hushed whispers and mild arguments from the two brothers, just out of earshot; which was quite far. Somewhere off in the building somewhere, just barely a mumble to him. He had spent his day elsewhere after that, only to return to find Dean beckoning him to the bedroom. Of course, he wouldn’t deny him. But he spoke to him nervously at first, but with a strange air of confidence and arousal.

“Cas…” he said, sitting down on the bed and patting it. “You know I love you, right?”

Did Dean love him? This was a bit new to him, but he had assumed something of the sort, so he nodded.

“Will you do something for me?”

“What is it?” Castiel asked, sitting beside him.

“I…I’d like to try something. You’re still really young and inexperienced with this sex thing…which really makes me want to try other things with you now, if that makes sense.”

“Not a lot, but go on…”

“Can I…invite someone to join us?”

Castiel raised a brow, considering it in his head. He was not jealous; he supposed if Dean wanted it…

“Are they trust worthy…?”

“Yeah, of course. You think I’d just bring in some random person? It’s okay. I know him.”

“Him…?”

“Yeah, him. And I promise you he’s good.”

After mulling it over, he nodded. Dean gave out a nervous laugh, going over to his dresser. “I want this to be a surprise…” he said, pulling out a bottle that Castiel knew well. He sat down on the bed again, facing him with a smile before he started to undo the angel’s tie. “Want to put this around your eyes, is that okay?”

Castiel was nervous at this, but he knew Dean; he knew this _was_ Dean and not a demon, or someone posing as such…he could trust him. Hesitant at first, he nodded, and closed his eyes as Dean slipped the dark fabric around his eyes, tying it behind him. He felt his fingers, nimble and quick on the buttons of his shirt and pants as he pulled away the clothing. Castiel soon found himself naked and vaguely aroused, but not enough to make too much of a difference. He could feel his cock twitching to life, and the slow pool of desire gathering in his belly and groin. He liked it when Dean took charge…

               

                Dean guided him onto the bed; pulling him so that he was laying splayed and against Dean’s chest. There was the sound of dull clicking before he heard the door open, and the sound of soft, padded footsteps across the floor. The bed sank in front of him, creaking with weight before he felt warm, large hands roaming his naked skin. Fingers sliding up his body before the sensation of lips upon his inner thighs, soft and gentle, with the delicate tickles of hair upon his flesh. He jolted slightly at these kisses, earning a reassuring whisper of, “It’s okay,” from Dean in his ear.

 

                There was the feeling of wet lips sucking deftly at the skin of his thighs, tongue darting out to lick at the bruised flesh. Castiel could feel arousal pooling deep in his belly; his cock felt hard now, fluid gathering at the tip as these motions continued. It was teasing, but at the same time enjoyable. His skin felt like it was starting to burn, nerves firing at every touch. The kisses and bites went to the inside of his hips before they stopped, bed shifting as whoever it was evidently pulled away. He felt strong hands on either side of his legs, pushing outwards and spreading them apart. There was silence before he heard Dean laugh, speaking, “Pretty, right? Touch him,” he commanded. There was silence again before the bed shifted, and he felt the hair tickling his upper thighs again. Stillness again before he felt wet fingertips prodding at his entrance, but not so much to enter. Just touching him there, causing the angel to shift his hips against the intrusion. He heard another laugh; or rather, a gasp of a laugh, but this time it was not from Dean.

 

                The fingers against him shifted, moving upward and catching against the rim of his muscle, pulling him open just slightly. He could feel the muscles protesting against him, but he himself tried to relax. He felt the digits moving; rubbing the area, causing small waves of pleasure shooting through his spine before he felt something very different; very wet. Slick and flexible as it’s tip ran against the open area of his passage, running along all those sensitive nerve endings. He felt himself shudder, head tilting back as he let out a noise of pleasure. A broken, choked and gasping moan that fled softly from his lips, as his pelvis shifted towards that writhing organ again. He soon realized, as he felt it enter, this was someone’s tongue. It writhed within him as the fingers caressed the slightly twitching flesh beneath their tips, sending stronger shockwaves of pleasure racing through him.

 

                It almost went unnoticed when hands- Dean’s hands- came to rest upon his pectorals, fingers coming to run along the hardening nubs of sensitive flesh. Dragging his nails across, pinching and rolling them between his fingers. Lips coming to rest upon his neck, kissing and biting with purpose. It left him gasping and trembling beneath him; hips shifting and thrusting against that tongue inside of him in desperation as he found it difficult to catch his breath.

“Isn’t he pretty?” he heard Dean ask again, lust clear in his voice now. “He may be an angel but deep down he’s just a wanton little slut.”

Castiel was taken aback by this, “E-excuse…me?” he managed to get out between breaths, annoyance still coming in clear.

“I mean it with love,” Dean said, kissing his neck again. “Not an insult. You are pretty…so pretty and so…tainted,” he said huskily, teeth sinking a bit hard into his neck before his tongue darted out to lick at the abused flesh. “Bet you never got anything like this up in Heaven, did you?”

Castiel could do nothing but shake his head, words caught in his throat as Dean’s hand started drifting down his body. “Like it when I touch you, don’t you?” he asked, fingers trailing down his stomach. He felt the muscles contract in response to the feather light touches. Felt Dean’s fingers come to his pubic bone, digits running along it softly before coming to his dripping cock. “Do you?” Dean asked again, never having gotten and answer. Castiel merely nodded, hips still jerking against whoever was below.

 

“You like him between your legs, baby? That feel good to you?” Dean asked again, his voice so rough and dripping with lust that Castiel felt it may take on a liquid form and spill everywhere.

“Mmm…y-yes..” he moaned, breath gasping and intercepted with pleasured cries he couldn’t help.

“How’s it feel, having a tongue in your ass? You like that?”

“G-good, yes,” he stuttered, finding it hard to form words.

Dean’s hand wrapped around his cock now, pumping languidly but just enough to get him crying out even more. “You want him? Want him to fuck you until you can’t even think? It’ll feel so good, baby. I bet he wants to fuck you too.”

 

                Castiel didn’t know who it was that was between his legs still, but he found that whoever it was, he did want them. Especially since Dean was giving the go ahead. At this point, he felt the tongue draw out of him, and the fingers at his rim start pushing in instead. Slowly and gently, but skillfully. They knew where to go, running along his inner walls and stimulating all the sensitive nerve endings there. He felt him move again, coming closer until he felt lips upon his own and they were not Dean’s. He could not yet identify them, but as he forced his tongue through his parted lips, Dean joined him. It was messy, wet and sloppy but it was a fairly interesting experience. He wasn’t sure who’s tongue was who’s, but he was trapped between the two of them, and trying to focus on both wasn’t all that easy. Within a moment the two had drawn away again, leaving silence for a moment before Dean spoke again, “Does he make you feel good?”

“Mmm,” he said, nodding and about given up on forming words.

“And you want him, right?”

“Mhhm,” he nodded, lips pressed together even as cries forced their way out.

 

                Before Dean could say anything else, Castiel felt a shock of pleasure race up his spine, shooting up into his vocal chords and forcing out a surprised, rough moan.

“Hey!” he heard Dean say, “Careful there. He’s still really sensitive. Don’t want him coming already,” he finished as Castiel felt the fingers behind him, loosening the tie around his head.

“Say hi, Cas” he said moments before slipping the tie over his head and tossing it elsewhere. Castiel opened his eyes, half lidded and dark before they widened and he let out a surprised gasp, trying to speak, “S-ahh!” he was cut off, letting out a loud cry before he could finished as fingers pressed down hard against what was, presumably, his prostate. “S-sam?” he managed to whine out finally, looking at the other man in front of him. It was, indeed, Sam… Pupils blown, hair mussed and very obviously naked though he could see not much from the waist down, as he was seated between his legs.

 

                Castiel was confused at first, not understanding why Dean would invite his own brother to something so personal and intimate, but he would begin to understand later. Sam gave him a smirk, speaking a rough and lust filled, “Hey,” before pushing against him again. The touch there left him unable to think; only moan deeply, intercepted by gasps and desperate whines as he bucked his hips against him.

 

                It wasn’t long before he felt Sam’s lips against his own, and he welcomed it with just some hesitation. Breath hot and heavy on his mouth as he kissed him, teeth somewhat roughly nipping at the thin skin of his lips. Moving downward from his mouth as he kissed down his jaw and neck, other hand coming to roam his torso. Fingers catching on the sensitive flesh of his erect nipple, deliberately so. Dean began to work on one side of his neck as well, lips suctioning and teeth biting before Sam came to join him in the same area. The sensation was almost painful if not overwhelming, as the two worked closer and closer to each other until he saw Sam’s teeth come in contact with Dean’s lower lip, biting at it until he pulled it into a deliberate kiss. Castiel was beginning to get the gist of just what was going on here…

 

                Dean mumbled against his brother’s mouth before pulling away and uttering a rough, “Fuck him,” command.

“Is that okay, Cas?” Sam asked, concern still filtering through the clouds of lust. Castiel merely nodded, as Sam withdrew his fingers and pushed his legs apart even further. Dean tossed the lubricant to him, before he set to spreading it on his fingers and then upon Castiel’s opening, making sure it was slick enough for entry. Castiel understood this. It took a few moments of Sam scissoring his entrance before he smeared the lube on his own cock, and he felt the slick, beginning intrusion of genitals much larger and much more different than Dean’s. He braced himself as Sam started to enter, breath hitching in his throat before he gasped and panted slightly. Sam was _big_ , and there was no denying that. He wasn’t quite used to such intrusion. In an attempt to soothe him, Dean gently kissed along his neck and jaw, whispering hushes and words of endearment and encouragement against his skin.

 

                It was a few moments before Sam had sheathed himself, and he felt his passage clamping around him in protest; desperately trying to remove such a large foreign object. He could hear Sam let out a shuddering, outward gasp at the sensations Castiel must have been inadvertently causing. Dean helped him through the pain by languidly running his fisted hand along his cock, causing him to be distracted by pleasure rather than pain. With a curious amusement obvious on his features, Dean laughed slightly, “His ass that good for you, Sammy?”

“He’s squeezing my dick with his ass.” Sam said, a bit strained. It caused another short laugh from Dean’s direction again, in response.

 

                Once Castiel managed to relax he could feel Sam start moving very slowly, forcing a muffled combination of a grunt and a moan. He was so tight around Sam, making the movements so much more sensitive to him; a mix of both pain and pleasure, though it was rapidly descending into pleasure rather than pain the more Sam moved inside of him. Dean worked with him again at that moment, hand pumping lightly on his cock as the other came to move upon his torso, fingers playing at his nipples again almost roughly.

 

                From then it was an upward spiral, Sam gaining his footing and Castiel loosening just enough for him to move. He found himself looking for something to hold onto; hands drifting until they found themselves at Dean’s forearm and the bed. He tightened and loosened his grip on the sheets and Dean’s arm with each thrust, as each thrust wrung a gasping moan from his lungs. He could hear the younger brother giving out soft, strained moans as he continued.

 

                Sam shifted himself, lowering his upper half so that he was at a different angle as he fucked him, lips coming to rest upon his before trailing downward again as he spoke and moaned against his jaw, “You’re so damn pretty,” he said, strained and intercepted with laborious and pleasured pants, “I’ve always wanted you…” Castiel wasn’t sure what to say, but he tried to form some semblance of words that only came out as a strained and trembling squeak. He wasn’t quite sure what he was even going to say, but as he did so he found one hand drifting towards that thick mane on Sam’s head while his hips rolled against the other male’s. This caused a surprised noise; a combination of a moan and a shout as he apparently had not expected Castiel to move.

 

                His hand left the youngest male’s hair as he shifted back again to gain more leverage, gripping Castiel’s hips as he pounded into him a bit harder. His sudden shift in movement sent him spiraling into absolute pleasure, cock striking hard against his prostate and causing a loud mewling moan to spill from his lips before speaking, “Oh fuck, Sam...!” he cried out, rocking his hips again and forcing the other’s cock against that deliciously sweet spot.

 

“God, Cas, the way you move is killing me…” he said, strained once again. Though Castiel found he could not respond again, desperately clinging onto everything he could reach again and shifting enough so that he could feel that pleasure over and over again. Though, admittedly, it was starting to get a bit overwhelming. That, coupled with Dean’s hand on his cock…he wasn’t sure how much longer he’d last. It wasn’t long, with Sam hammering down on this spot that he started to feel that of an impending orgasm, coming slow and driving him mad with unbelievable pleasure. He felt incredibly tight, legs spreading further from reflex and back arching, moaning choked and gasping.

“He’s so damn close, Sam. Bring it home,” Dean said, pumping a bit faster and tighter on his cock now, and felt as it built up slowly, and slowly until it finally burst. The noise he made was deep, rough and choked out like he could barely breathe as he gasped and tried to ride his way through the orgasm. Dean kept touching him, and Sam kept hitting his prostate. It was overwhelming and he trembled, thighs shaking around Sam’s body as his fingers clutched so tightly he knew he was drawing blood on Dean’s arm from his nails.

 

                He dully registered the wetness spurting from his member, cascading onto both his stomach and Dean’s hand, dripping downward until it was a mess of pearlescent fluids slicking his fingers. He had only just begun to calm down when he dully heard Sam cry out through the ringing in his ears and the presence of something hot and wet shooting through his insides. His body was slumped hard against Dean’s, breathing still heavy and eyes closed peacefully as he tried to recover from that intense euphoria. He felt Dean run a clean hand through his hair, stroking back what had fallen out of place in the rendezvous. But little did he realize at the time, this was not the end.

                Dean warned him as he moved, setting him gently down on the bed and scooting beside him as Sam pulled away. He watched with heavy lidded, tired eyes as Dean’s legs spread out as much as they could and he laid against the headboard, and Sam grabbed the bottle of lube from where it rested on the bed. Castiel was surprised it was still there. Castiel could see now just how hard Dean was. He had felt it vaguely on his back while he was pressed against him, but Dean was rock solid and his cock was dripping wet with need. Sam crawled forward, low on the bed as he spread the lube on his fingers again and pushed forward, and Castiel watched as they disappeared between Dean’s legs and soon realized they were most definitely inside the eldest brother after he had worked against him for a moment.

 

                He watched as Sam lowered his head, tongue darting out to lap at Dean’s cock; running it along the underside of the shaft as it swirled along the head. He watched him, with a mild amount of jealousy and desire, and also with curiosity and an attempt to study just what Sam was doing. But Castiel felt out of place; watching Sam on Dean’s cock, fingers buried deep inside of him as Castiel merely laid there and did nothing. He could _not_ let just Sam bring him to completion; not while he was there. After a moment of watching Dean lay there, breath panting with pleasured moans and hips shifting against Sam’s fingers and his tongue, Castiel moved.

 

                Languidly crawling across the small expanse he had to of the bed, lowering himself until he was at Dean’s cock, who at the moment had his eyes closed and was completely oblivious. He joined Sam at this point, licking tentatively at the flesh; finding it tasting of skin and smelling strongly of male musk and arousal. This earned a surprised gasp from the eldest brother, eyes shooting open and looking down at them as he mumbled Castiel’s name in a flurry of curses. He made his way along what he could, sometimes running into Sam’s tongue on the way. He decided at this point to wrap his lips around what he could; around the head of Dean’s cock.

 

                He bobbed very slightly as his tongue swirled inside of his mouth, around the sensitive nerve endings, while Sam focused on what was now exposed. Paying special attention to the underside, fingers still working within his brother. Castiel could not tell if Dean was close or not, but he did hear his breathing pick up and his hips move more desperately. It was when he experimented that he got quite a surprise. He dipped his tongue hard against the slit of his cock, tasting the salty precum at it’s source before he was met with something with far much more volume. Dean came against his tongue at that moment, some of it hitting the back of it throat but most of it coating his mouth. He was too surprised, not able to react in time and most of it ran past his lips and dripped back down onto the softening organ.

 

                He pulled away, licking at his lips in curiosity as it dribbled down from his mouth, and he realized it was still running down his chin. After Sam had made his way along Dean’s cock, effectively cleaning what had dripped from Castiel’s lips with his tongue, Sam, too, drew away. Coming to Castiel and managing to get him on his back, kissing at his jaw until his tongue came to the wetness on his chin. Lapping it into his own mouth before he came to the angel’s, tongue running along his lower lip before pushing in and running along his own. Licking at the organ and working with him, as he still tasted of semen.

 

                Once Dean was sated, he managed to move, coming to lay next to Castiel as he placed a gentle kiss upon his shoulder, neck, cheek, and so on, before moving to his lips and joining Sam. He too pushing his tongue forward and tasting himself on Castiel’s tongue, working with both his and Sam’s before pulling away and lazily laying next to him.

 

                Despite the fact that Castiel was still a mess, they fell into a sort of tangled pile, both Sam and Dean laying against him on their sides as Castiel laid on his back.

“I’ve had one, but not two pretty boys at my cock at once,” Dean mumbled against his neck, voice obviously sleepy and exhausted. But now that Castiel was free from the haze of both sex and orgasm, his mind started to work and he had to question it….

“Are you two…in a relationship?” he asked, curiously.

“Relationship? Nah. More like friends…brothers, with benefits.” He mumbled, and it was then that he really explained everything to Castiel.

 

                He had been doing this with Sam for a long time, and evidently liked to watch his brother fuck his boyfriends or girlfriends, as well as having an occasional fuck or two on the side with just the two of them. Despite the fact that he was Dean’s lover and not Sam’s, and Dean really had no romantic feelings for Sam, Castiel felt comfortable and right in the both of their embrace. He laid there as the both of them eventually fell asleep against him, limbs tangled like a web, trapping him in the warmest embrace he’d ever known. Castiel wasn’t one to sleep, but he was tired after this, and he too managed to drift into a slumber. He’d clean up in the morning.


End file.
